Protocatechuic Acid → (2S)-2-[(3,4-dihydroxybenzoyl)amino]-N-(2,5-dimethoxyphenyl)-N'-trityl-pentanediamide

HRID 1860340Notes

Reaction equation

C1C2C(CO[C:16]([NH:18][C@H:19]([C:44]([NH:46][C:47]3[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=3[O:55][CH3:56])=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:17])C3C(=CC=CC=3)C=2C=CC=1.[OH:57][C:58]1[CH:59]=[C:60]([CH:64]=[CH:65][C:66]=1[OH:67])C(O)=O>>[OH:57][C:58]1[CH:59]=[C:60]([CH:64]=[CH:65][C:66]=1[OH:67])[C:16]([NH:18][C@H:19]([C:44]([NH:46][C:47]1[CH:52]=[C:51]([O:53][CH3:54])[CH:50]=[CH:49][C:48]=1[O:55][CH3:56])=[O:45])[CH2:20][CH2:21][C:22](=[O:43])[NH:23][C:24]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:17]

Participants

Reactant 2

HCID 72Protocatechuic Acid

HCID 22976128N-[Nalpha-(9-fluorenylmethoxycarbonyl)-Ndelta-trityl-L-glutaminyl]-2,5-dimethoxyaniline

Product 1

HCID 504848(2S)-2-[(3,4-dihydroxybenzoyl)amino]-N-(2,5-dimethoxyphenyl)-N'-trityl-pentanediamide

Procedure

The title compound was prepared from N-[Nα-(9-fluorenylmethoxycarbonyl)-Nδ-trityl-L-glutaminyl]-2,5-dimethoxyaniline (531 mg, 0.7 mmol, example 82, step A) as described for example 82 (step B) using 3,4-dihydroxybenzoic acid (164 mg, 1.1 mmol) instead of caffeic acid. The crude material was purified by flash chromatography using first 10% then 30% EtOAc/CH2Cl2 containing 1% AcOH. The title compound was obtained as yellow crystals (164 mg, 35%).

Workup

customThe crude material was purified by flash chromatography

Sources & evidence

ORD record: ord-6215422706014a098999444c7f0121f2
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528655B1

Reaction notes

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